Interpretive Summary: The metabolic fate of the phytochemical pterostilbene was investigated. Pterostilbene, at a dose of 20 mg/kg body weight, was administered intravenously to Male Sprague-Dawley rats. Analysis of serum and urine samples by HPLC showed the presence of a pterostilbene-glucoside metabolite. Further studies were conducted to determine the anti-cancer, anti-inflammatory, anti-oxidant, and analgesic activities of pterostilbene. Pterostilbene demonstrated concentration - dependent (1-100 ug/mL) inhibitory activity in the five cancer cell lines (malignant melanoma, colorectal carcinoma, hepatocellular carcinoma, breast adenocarcinoma, and prostate adenocarcinoma) examined. Its anti-inflammatory activity was studies in vitro by inducing inflammation in chondrocytes with interleukin-1B (IL-1B) followed by treatment with pterostilbene (1-100 ug/mL). Pterostilbene showed decreased levels of various mediators released during inflammatory events (MMP-3, sGAG, and TNF-a) compared to controls. Pterostilbene demonstrated a concentration-dependent anti-oxidant capacity, measured using the ABTS method. Analgesic activity was demonstrated using hot-plate and tail-flick tests in mice after administration of pterostilbene (50 mg/kg body weight). This study is the first, to our knowledge, to delineate the metabolism of pterostilbene.